2-Amino-2-phenylethan-1-ol → (R)-N2-(Boc)-N5-(Cbz)-(S)-N-(2-hydroxy-1-phenylethyl)ornithine amide

HRID 366052

Reaktionsgleichung

Reaktionsgleichung von HRID 366052
[N+](C1C=CC=CC=1O[C:11](=[O:35])[C@@H:12]([CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([O-])=O.[CH:36]1[CH:41]=[CH:40][C:39]([C@H:42]([NH2:45])[CH2:43][OH:44])=[CH:38][CH:37]=1>C(Cl)Cl>[C:14]([NH:13][C@H:12]([C:11]([NH:45][C@H:42]([C:39]1[CH:40]=[CH:41][CH:36]=[CH:37][CH:38]=1)[CH2:43][OH:44])=[O:35])[CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15]

Komponenten

4

Edukt 2

HCID 1347972-Amino-2-phenylethan-1-olHCID 54461433Nalpha-Boc-Ndelta-Cbz-(R)-ornithine o-nitrophenyl ester

Produkt 1

HCID 131722056(R)-N2-(Boc)-N5-(Cbz)-(S)-N-(2-hydroxy-1-phenylethyl)ornithine amideAusbeute 84,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Prepared according to the method described in Example 4(b) above from Nα -Boc-Nδ -Cbz-(R)-ornithine o-nitrophenyl ester (4.0 g; 9.22 mmol; see Example 4(a) above) and (S)-(+)-phenylglycinol (1.26 g; 9.22 mmol; 1 eq.) and CH2Cl2 (160 mL). The reaction mixture was stirred overnight and then washed with saturated aqueous KHSO4, saturated aqueous Na2CO3, brine, dried with Na2SO4, filtered and concentrated to dryness. The residue was triturated with ether to obtain 3.8 g of the sub-title compound as a white solid.

Aufarbeitung

  1. customPrepared
  2. washwashed with saturated aqueous KHSO4, saturated aqueous Na2CO3, brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-8cd4c887def642c489315ee6a3322969
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127414

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